Trifluoroacetic acid → HCID 23512193, compound

HRID 354406Notes

Reaction equation

HRID 354406 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH2:10][CH:9]1[CH2:22][O:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[O:13][CH:11]1[CH2:12][NH:8][CH:9]([CH2:22][O:23][C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69333033Methyl 4-(1-(tert-butoxycarbonyl)-4-(2,4-difluorophenoxy)-2-pyrrolidinyl methoxy]benzoate

Product 1

HCID 23512193HCID 23512193, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 4-[1-(tert-butoxycarbonyl)-4-(2,4-difluorophenoxy)-2-pyrrolidinylmethoxy]benzoate (529 mg, 1.15 mmol) in CH2Cl2 (5 ml) was added TFA (5 ml). The mixture was stirred overnight. The mixture was concentrated in vacuo and the residue was made basic by the addition of sat. NaHCO3. The mixture was extracted with CHCl3 (2×100 ml). The extracts were dried over K2CO3 and evaporated to give methyl 4-[4-(2,4-difluorophenoxy)-2-pyrrolidinylmethoxy]benzoate (385 mg, 92%) as a yellow oil. 1H-NMR (CDCl3) δ1.89-1.95 (m, 1 H), 2.28-2.35 (m, 1 H), 3.09 (dd, J=12.5, 4.9 Hz, 1 H), 3.33 (d, J=12.5 Hz, 1 H), 3.60 (m, 1 H), 3.86 (s, 3 H), 4.10 (d, J=5.6 Hz, 2 H), 4.84 (m, 1 H), 6.73-6.89 (m, 3 H), 6.91 (d, J=8.5 Hz, 2 H), 7.96 (d, J=8.5 Hz, 2 H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was made basic by the addition of sat. NaHCO3
  3. extractionThe mixture was extracted with CHCl3 (2×100 ml)
  4. dry with materialThe extracts were dried over K2CO3
  5. customevaporated

Sources & evidence

ORD record
ord-ec0db9cf8fed45ae9fd1d3084a7704fc
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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